Peroxy-acid oxidation of NN-disubstituted aminotetrafluoro-, amino-3-chlorotrifluoro-, and amino-3,5-dichlorodifluoro-pyridines

Abstract

Peroxy-acid oxidation of NN-disubstituted 4-aminotetrafluoropyridines occurred with rearrangement of the expected intermediate N-oxide to give the NNO-trisubstituted hydroxylamines. The 2,4-bis-(NN-disubstituted amino)trifluoropyridines gave the 2-mono-N-oxide only. The oxidation of NN-dialkylamino-3-chlorotrifluoro and -3,5-dichlorodifluoropyridines was also studied and the influence of the amino- and methoxy-groups and of the different halogens on the result is discussed. The observed behaviour is compared and contrasted with that of the analogous derivatives of pentachloropyridine, and the differences in the behaviours of the polyhalogenated pyridines are rationally explained.